{[(2S,3S,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester

Base Information

• Chemical Name: {[(2S,3S,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester
• CAS No.: 868526-30-1
• Molecular Formula: C₂₇H₃₅N₃O₆
• Molecular Weight: 497.591
• Mol file: 868526-30-1.mol

Synonyms:{[(2S,3S,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester

Chemical Property of {[(2S,3S,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {[(2S,3S,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester

There total 12 articles about {[(2S,3S,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylpyrrolidine-2-carboxylic acid (858367-12-1) + glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) → {[(2S,3S,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester (868526-30-1)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1002/anie.200462497

Reference yield:

(2S,3S)-2-(benzyloxy)-3-methylpentanal (858366-80-0) → {[(2S,3S,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester (868526-30-1)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / 16 h / 20 °C

2: methanesulfonyl chloride; ethyldiisopropylamine / CH₂Cl₂ / -70 - 20 °C

3: triethylamine; AgOAc / acetonitrile / 5 h / 20 °C

4: LiOH / 1,2-dimethoxy-ethane; H₂O / 0 °C

5: diethyl cyanophosphonate; triethylamine / dimethylformamide / 16 h / 20 °C

With lithium hydroxide; diethyl cyanophosphonate; silver(I) acetate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Henry reaction;

DOI:10.1002/anie.200462497

Reference yield:

(2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol (858366-85-5) → {[(2S,3S,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester (868526-30-1)

Guidance literature:

Multi-step reaction with 6 steps

1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 5 h / -70 - -60 °C

2: triethylamine / 16 h / 20 °C

3: methanesulfonyl chloride; ethyldiisopropylamine / CH₂Cl₂ / -70 - 20 °C

4: triethylamine; AgOAc / acetonitrile / 5 h / 20 °C

5: LiOH / 1,2-dimethoxy-ethane; H₂O / 0 °C

6: diethyl cyanophosphonate; triethylamine / dimethylformamide / 16 h / 20 °C

With lithium hydroxide; oxalyl dichloride; diethyl cyanophosphonate; silver(I) acetate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 2: Henry reaction;

DOI:10.1002/anie.200462497

upstream raw materials:

(2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylpyrrolidine-2-carboxylic acid

glycine ethyl ester hydrochloride

(2S,3S)-2-(benzyloxy)-3-methylpentanal

(2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol